Chief of Staff

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OuterSignal

WebsiteLinkedInAll Job Openings

1 - 10 employees

☁️ SaaS

🤝 B2B

🛍️ eCommerce

SaaS • B2B • eCommerce

OuterSignal is a customer intelligence SaaS platform that helps eCommerce and direct-to-consumer brands identify high-value customers, influencers, and strategic B2B leads from their order data in real time. It provides VIP detection, deep audience segmentation, persona and demographic analytics, and one-click exports to ad platforms and CRMs so brands can personalize marketing, uncover retail or partnership opportunities, and act on insights immediately. The product integrates with merchants' stacks (e. g. , Shopify, Meta, CRMs) and emphasizes real-time alerts, lookalike building, and segment activation to boost LTV and campaign performance.

📋 Description

• Be the right hand to the VP of Operations — partner with them day-to-day to turn strategy into execution and own the things that fall between the cracks • Act as a trusted thought partner and sounding board to the VP of Operations — and, more broadly, to the CEO and executive team — to help think through strategy, pressure-test decisions, and frame the trade-offs that matter • Protect executive focus — filter and triage what reaches the VP of Operations and CEO, surface bottlenecks early, and keep the team’s attention on the decisions that matter most • Own company planning — run quarterly and annual goal-setting (OKRs), translate it into an operating plan the team executes against, and define and track the KPIs and dashboards that keep everyone honest about progress • Partner with finance to work backwards from the model — connecting targets, headcount, and spend to the operating plan and flagging where reality is drifting from plan • Run the company’s operating cadence: exec meetings, weekly standups, reviews — set agendas, capture decisions, and chase every action to done • Drive cross-functional initiatives end-to-end, like integrating our recent acquisition (Monocle) into our stack and operations, and standing up consistent company-wide process • Be a trusted point of contact for investors, partners, and vendors — own these relationships day-to-day so leadership never becomes the bottleneck, and carry board meetings and fundraises from prep through follow-through • Take on the big company-building projects ahead of us — starting with SOC 2 certification, a major unlock for enterprise trust and larger deals • Power our rapid hiring — coordinate interview loops and sharpen the recruiting process as we grow the team fast • Lead special projects across the operations org — including driving AI adoption across technical and non-technical teams

🎯 Requirements

• 3–7+ years in a Chief of Staff, startup operations, business operations, or founder’s-office role at a high-growth company — you’ve done the work, not just advised on it • A hands-on operator, not a consultant — you build process out of chaos and automate yourself out of the busywork • Strong business and financial fluency — comfortable in a model, setting targets, and reasoning about the numbers behind the plan • AI-native: you reach for AI tools to move faster by default, and you can drive that adoption across a team • Exceptionally organized and systems-minded, with crisp written communication and the presence to run a room of senior people • Bonus if you’ve integrated an acquisition, stood up SOC 2, or supported a fundraise • Most importantly: you want ownership. You like to move fast, solve “figure-it-out” problems, and aren’t afraid of messy early-stage work.

🏖️ Benefits

• Massive upside: Meaningful equity in a venture-backed company defining a new SaaS category • A product that delivers — genuinely memorable customer outcomes, with case studies that speak for themselves. • A team that moves — a leadership group operating with urgency and building toward something significant.